IUPAC name: (9Z,12R)-12-Hydroxyoctadec-9-enoic acid
CAS Number: 141-22-0
Chemical formula: C18H34O3
Molar mass: 298.461 g/mol
Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid is a fatty acid.
Ricinoleic acid is an unsaturated omega-9 fatty acid and a hydroxy acid.
Ricinoleic acid is a major component of the seed oil obtained from mature castor plant (Ricinus communis L., Euphorbiaceae) seeds or in sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae).
About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.
Production
Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil.
The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888.
Use
Sebacic acid ((CH2)8(CO2H)2), which is used in preparing certain nylons, is produced by cleavage of ricinoleic acid.
The coproduct is 2-octanol.
The zinc salt is used in personal care products such as deodorants.
Biological activities
Ricinoleic acid exerts analgesic and anti-inflammatory effects.
Ricinoleic acid specifically activates the EP3 prostanoid receptor for prostaglandin E2.
Ricinoleic acid acts as a specific algicide for the control of cyanobacteria (formerly called blue-green algae).
Ricinoleic acid is the primary constituent of castor oil, which comes from the seeds of the castor bean plant (Ricinus communis L.).
Approximately 85-90% of castor oil consists of ricinoleic acid.
Ricinoleic acid should be noted that with such a high percentage of ricinoleic acid in castor oil, essentially it is a technical grade product—something that rarely happens in nature with plant oils. India is by far the largest producer of castor oil followed by China, Brazil, Thailand, Ethiopia, and Paraguay.
Ricinoleic acid has a unique molecular structure attributed to the hydroxyl group located in the middle of the unsaturated chain. In the triglycerol form, hydrogen bonding occurs with the hydroxyl groups resulting in greater viscosity than in other oils.
For this reason, castor oil is a superior lubricant as compared to other vegetable oils.
In addition, the hydroxyl group—only separated from the double bond by a methylene group—imparts increased oxidative stability, thereby providing castor oil a longer shelf-life.
Furthermore, this structural feature also affects the solvation properties and miscibility of ricinoleic acid.
Unlike most fatty acids, ricinoleic acid is soluble in more polar solvents (e.g., alcohols).
Castor oil is used in many diverse areas including cosmetics, coatings, detergents, food, medicine, and plasticizer technology.
Ricinoleic acid is traditional use as a household remedy has been known for many years to treat constipation, condition hair and skin, and alleve arthritis and muscle pain.
During the middle and early twentieth century In the United States, many parents used castor oil to deter their children from misbehaving.
Ricinoleic acid was common to threaten, “If you don’t behave, you are going to have to take your castor oil.”
This was even famously portrayed in the cartoon series Tom and Jerry in a 1953 episode.
In cosmetics, castor oil is found in variety of products including hair preparations, soaps, and skin ointments.
In addition, one of the largest applications of castor oil in personal care is in lipstick preparations.
In fact it has been quoted: “Castor oil is one of the stalwarts of lipstick formulation since it creates the highest gloss of all natural oils when applied to the skin.
Ricinoleic acid is occlusive, water-repellant, tacky, and very protective to the skin.”
Ricinoleic acid is found in high concentrations in lipsticks.
There are also a number of ricinoleic acid derivatives used in a variety of personal care formulations including cetyl ricinoleate, ethyl ricinoleate, glyceryl ricinoleate, and zinc ricinoleate as well as polyethoxylated esters of ricinoleic acid. Overall, these materials are deemed safe for use in cosmetics.6 More than likely, the broad use of castor oil in cosmetics comes from the compatibility of ricinoleic acid with polar and nonpolar ingredients.
Ricinoleic acid is an unsaturated omega-9 fatty acid that naturally occurs in mature Castor plant (Ricinus communis L., Euphorbiaceae) seeds or in sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.
Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil.
Ricinoleic acid exerts analgesic and anti-inflammatory effects. The zinc salt is used in personal care products, such as deodorants.
Ricinoleic acid (RA) is an important raw material for plasticizers, emulsifiers, and nanomaterials. In this work, a green and efficient method was developed for RA production.
Results showed that Lipozyme TLIM can be used as a novel biocatalyst to catalyze the hydrolysis of castor oil (CO) for RA preparation.
Response surface methodology (RSM) was used to evaluate and optimize the effects of reaction variables on the hydrolysis of CO.
Reaction conditions were optimized as follows: 41.3 °C, enzyme load 8.9%, 39.2 h, and 40:1 molar ratio of water to oil.
Under these optimized reaction variables, the maximum hydrolysis ratio of CO (96.2 ± 1.5%) was obtained.
The effect of hydrolysis variables on the reaction was as follows: enzyme load > hydrolysis time > temperature.
In conclusion, this is a green, simple, and efficient method for RA preparation and can provide a good alternative method for RA industrial production.
Introduction
Ricinoleic acid (RA), also known as cis-12-hydroxy-9-octadecenoic acid, is the only industrial fatty acid containing a hydroxy group in nature and can be used as raw material for skin care products, plasticizers, emulsifiers, lubricants, and nanomaterials.
Castor oil (CO) is one kind of nonedible oil derived from the plant seeds of Ricinus communis.
RA is the main fatty acid of CO, and the content of RA is ~90% in CO.
Therefore, the preparation of RA from CO has been considered an attractive method.
In previous reports, RA was produced by the hydrolysis of CO, and acids, bases, and enzymes were used as catalysts.
When acid and base were used as catalysts, estolide byproducts easily formed by condensation between the hydroxyl and the carboxyl in RA.
RA products with bad odor and color were often obtained using high temperatures and chemical catalysts.
These factors made enzymes more suitable for RA preparation by the hydrolysis of CO.
Recently, some enzymes have been used to catalyze the hydrolysis of triacylglycerols for the preparation of fatty acids, especially for those fatty acids with unsaturated bonds and hydroxyl groups.
For example, the lipase from oat seeds was firstly used to catalyze the hydrolysis of CO.
After that, other lipases, Rhizopus oryzae lipase [18], Pseudomonas aeruginosa KKA-5 lipase, porcine pancreatic lipase (PPL), and castor bean lipase [19], were also used as catalysts for RA preparation by the hydrolysis of CO.
Among them, the maximum hydrolysis ratio of CO was ~90% for 96 h using the purified lipase from Pseudomonas aeruginosa KKA-5 as catalyst and 10 mM CaCl2 to stabilize the lipase.
Khaskhelia et al. also studied the hydrolysis of CO using Rhizopus oryzae lipase, achieving a similar hydrolysis ratio of CO (90%).
However, these previous methods showed some disadvantages including their time-consuming nature, low hydrolysis ratio, and pH requirements.
Therefore, a green and efficient method to prepare RA was more popular.
In this work, Lipozyme TLIM (lipase from Thermomyces lanuginose) was used as a novel biocatalyst for RA preparation by the hydrolysis of CO.
Several immobilized lipases were screened and compared.
The effect of reaction conditions (hydrolysis temperature, enzyme load, molar ratio of water to oil, and hydrolysis time) on the hydrolysis of CO was investigated and optimized by RSM.
Melting Point: 5.5 °C
Density: 0.945 g/cm3
XLogP3-AA: 5.7
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 15
Exact Mass: 298.25079494
Monoisotopic Mass: 298.25079494
Topological Polar Surface Area: 57.5 Ų
Heavy Atom Count: 21
Complexity: 261
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid is a fatty acid.
KEYWORDS:
141-22-0, (RZ)-12-Hydroxyoctadec-9-enoic acid, Ricinic acid, Castor oil acid, 12-Hydroxy-cis-9-octadecenoic acid, Kyselina ricinolova, (9Z12R)-12-hydroxyoctadec-9-enoic acid, D-12-Hydroxyoleic acid, Nouracid CS 80, UNII-I2D0F69854
Ricinoleic acid is one of the castor oil derivatives used in many products by various industries.
Ricinoleic acid is an unsaturated omega-9 fatty acid and a hydroxy acid, a major component derived from the castor seeds.
Castor oil is also described as ricinoleic acid triglyceride which has the availability of hydroxy functionality of fatty acid for up to 70-90%.
Ricinoleic acid has three functional groups which define its versatility and its importance in producing castor oil-based products.
For example, carboxylic group.
This group can be led to produce esterification products.
The single point of unsaturation can be modified by hydrogenation, epoxidation and vulcanization.
The carboxylic group transforms castor oil through reactions like esterification and amidation.
The existence of a double bond transforms the castor oil through hydrogenation, carbonylation and epoxidation.
The hydrogenation process transforms the liquid ricinoleic acid into a semi-solid saturated state.
The semi-solid saturated ricinoleic acid is useful in resin or polymer mixtures because the oil has a high melting capacity, good storage quality, taste and odour.
The functional group hydroxyl can be acetylated, alkoxylated or removed by dehydration to increase unsaturation of the castor oil at carbon-12.
Catalytic dehydration forms a new double bond in the link of ricinoleic acid which results in a conjugated acid.
This type of change helps in rapid drying, excellent colour retention, flexibility and water retention for coatings.
Ricinoleic acid is derived from castor oil through the process of hydrolysis.
For industrial use, mostly it is produced by saponification or fractional distillation of hydrolyzed castor oil.
As a hydroxy fatty acid, ricinoleic oil is used in oleochemical industries.
These chemicals are similar to petrochemical commodities and can be used for various chemical applications.
Castor oil is an important bio-based raw material for industrial applications.
Ricinoleic acid is deemed as a suitable renewable resource for chemical reactions, modifications and transformations.
Ricinoleic acid, an important castor oil derivative, is used in pigments, printing ink and textile finishing.
Ricinoleic acid is also added in turkey red oil, dry-cleaning products and detergent formulations. Ricinoleic acid is different kinds of derivatives are like ricinoleyl alcohol, methyl ricinoleate, azelaic acid, and ricinenic acid are used as plasticizer and emulsifier.
Ricinoleic acid from castor oil is considered safe to use in skin products.
Castor oil creates a super gloss on the skin, making products water-proof while protecting the skin.
For these products, ricinoleic acid and its derivatives are used as an anticaking agent, deodorant agent, emulsion stabilizer, opacifying agent, skin conditioning agent, cleansing agent, emulsifying agent, and viscosity increasing agent of course as it has the greater viscosity than other oils which makes it superior lubricant when compared to other plant-based oils.
The oxidative stability, therefore, provides longer shelf life for its products.
Ricinoleic acid is soluble in polar solvents, unlike other fatty acids.
The derivatives used in cosmetics are Zinc Ricinoleate, Glyceryl Ricinoleate, Ethyl Ricinoleate, Cetyl Ricinoleate, Glycol Ricinoleate, Methyl Ricinoleate, Isopropyl Ricinoleate, Potassium Ricinoleate, Sodium Ricinoleate and Octyldodecyl Ricinoleate.
The functions of ricinoleic acid provide many possibilities for it in several products depending on its usage. There are different processes to make ricinoleic acid usable for different products.
Ricinoleic acid is a naturally occurring 12-hydroxy fatty acid.
Ricinoleic acid constitutes about 90% of the fatty acids in castor oil.
Ricinoleic acid can serve as a substrate for the synthesis of conjugated linoleic acids.
Ricinoleic acid is considered safe and non-toxic as a food constituent in humans, up to a daily intake of 2.5 grams per day.
In high doses, castor oil has a laxative effect.
Ricinoleic acid is an unsaturated fatty acid, also referred to as 12-hydroxy-9-cis-octadecenoic acid.
Ricinoleic acid is derived primarily from castor oil, in which it accounts for up to 90 percent of total triglyceride content.
Sold as a yellowish, viscous liquid, ricinoleic acid serves many important purposes in the manufacturing of personal care products, pharmaceuticals, lubricants and more.
Lubricants and Greases: Emulsifier, Ester
Metal Working Fluids: Intermediate
CASE: Carrier and Dispersing Agent
Product Characteristics and Potential Applications
Acme-Hardesty ricinoleic acid has a minimum acid value of 175, a minimum saponification value of 180 and an iodine value between 80-91. Under normal storage conditions, it has a shelf life of up to six months after the date of manufacture.
Some applications in which ricinoleic acid is used include lubrication and grease production, which, in its esterified form, it serves as an emulsifier.
Ricinoleic acid is also used as a carrier and dispersing agent in paints and dyes, and as an intermediate in metalworking fluids.
Ricinoleic acid has strong antibacterial properties, which contributes to the benefits of castor oil-based skincare products.
The oil obtained from the seeds of the castor oil plant Ricinus communis is one of the oldest drugs known to man.
Castor oil is known primarily as an effective laxative; however, it was also used in ancient times with pregnant women to induce labor.
Aside from getting rid of acne, castor oil also helps detoxify the skin.
Ricinoleic acid helps break up the oils that clog glands and pores on the face. Only now, have scientists at the Max Planck Institute for Heart and Lung Research succeeded in unravelling the mysteries of the action mechanism.
Ricinoleic acid released from the oil in the intestine, is responsible for the analgesic and anti-inflammatory effects.
Ricinoleic acid was discovered, that G protein-coupled receptors, a large group of receptors in the body involved primarily in transmitting signals in cells.
Hundreds of receptors were systematically turned off, and then the reaction of the cells to ricinoleic acid was tested.
Ultimately, was succeeded identified the key receptor with the name EP3.
There was concluded that after being released from the castor oil, the ricinoleic acid is first of all absorbed by the body via the intestinal mucosa; the EP3 receptor then becomes active on the muscle cells of the intestine and uterus, which in turn stimulates intestinal activity.
Applications
Primary uses include, coatings, plastics, inks and cosmetics.
Poly (anhydrides) is hydrolytically degradable polymers which have been used as vehicles for controlled delivery of drugs. A new class of biodegradable polyanhydrides based on ricinoleic acid has been synthesized
Ricinoleic acid is effective in preventing the growth of numerous species of viruses, bacteria, yeasts, and molds.
Ricinoleic acid's successful as a topical treatment for ringworm, keratoses, skin inflammation, abrasions, fungal-infected finger- and toenails, acne, and chronic pruritus (itching). Generally, for these conditions the affected area is wrapped each night in a castor oil-soaked cloth.
Ricinoleic acid is used also as a bactericide.
Hence, washing wounds with ricinoleic acid at prescribed dilution levels is sometimes recommended.
Ricin acts as a blood coagulant
Macrolactones and polyesters can be derived from ricinoleic acid
Ricinoleic acid has been used in contraceptive jellies
Ricinoleic acid used in soaps, amine compounds, esters in cutting oils, industrial lubricants, emulsifiers, metal working compounds.
Ricinoleate soaps have been patented as algaecides for aquaculture systems.
Ricinoleic acid used in dispersion of pigments and dyes.
Ricinoleic acid used in resins, thermosetting acrylics and non-drying plasticizing esters.
Quaternary ammonium compounds based on ricinoleates and hydroxy stearates have been used in for cosmetics skin and hair care, personal products, germicides and textile processing agents.
Synonyms:
(R,Z)-12-Hydroxyoctadec-9-enoic acid
Ricinic acid
Castor oil acid
12-Hydroxy-cis-9-octadecenoic acid
Kyselina ricinolova
(9Z,12R)-12-hydroxyoctadec-9-enoic acid
D-12-Hydroxyoleic acid
Nouracid CS 80
UNII-I2D0F69854
Kyselina 12-hydroxy-9-oktadecenova
l'acide ricinoleique
NSC 281242
CHEBI:28592
12-Hydroxyoctadeca-9-enoic acid
12R-hydroxy-9Z-octadecenoic acid
MFCD00084840
12-D-Hydroxy-9-cis-octadecenoic acid
I2D0F69854
12-Hydroxy-9-octadecenoic acid
(R)-12-Hydroxy-cis-9-octadecenoic acid
DSSTox_CID_21567
DSSTox_RID_79777
DSSTox_GSID_41567
Riconoleic acid
Ricinusoleic acid
Acide ricinoleique
[r]-12-hydroxy-cis-9-octadecenoic acid
CAS-141-22-0NCGC00161336-02
(cis,R)-12-hydroxyoctadec-9-enoic acid
Ricinolsaeure
ricinoleic-acid
HSDB 5634
NCGC00181322-01
EINECS 205-470-2
VESPULA PENSYLVANICA B708568K062
(9Z,12R)-12-Hydroxy-9-octadecensaeure
(R-(Z))-12-Hydroxy-9-octadecenoic acid
(Z,12R)-12-hydroxyoctadec-9-enoic acid
Ricinoleic acid, >=99%
SCHEMBL18144
Flexricin 100 (Salt/Mix)
BML2-F10
CHEMBL3186422
DTXSID0041567
HY-N6070A
HY-N6070
12-Hydroxy-9(Z)-octadecenoic acid
Tox21_113406
Tox21_301098
LMFA02000184
ZINC12954494
12R-Hydroxy-9-cis-octadecenoic Acid
AKOS016005826
(9Z)-(12R)-Hydroxyoctadecenoic acid
DB02955
(Z,R)-12-hydroxyoctadec-9-enoic acid
12-OH 9c-18:1
NCGC00161336-01
NCGC00161336-03
NCGC00181089-01
NCGC00254998-01
(9Z)-12-Hydroxy-9-octadecenoic acid #
AS-65782
CS-0032307
CS-0204122
R0027
C08365
Ricinoleic acid, Vetec(TM) reagent grade, 80%
A885691
Q424484
W-108189